Sorry for resurrecting an older thread. But I was inspired by the discussion here...
So I just did my first IRA withdrawal with 100% withholding, which is the safe harbor amount for 2020 based on 2019 actual tax. I'll replace the IRA withdrawal from savings within 60 days, so it's a non-taxable rollover. Result is: I get the safe-harbor amount in the form of withholding and still use taxable funds to pay tax, almost all of which results from a large Roth conversion.
I'd like to do this every year. But I'm concerned about the "one rollover per 12 months rule." So I've been researching this. I know that the clock starts ticking on the day of the original distribution, which is today 12/30/2020. So I guess I could do a similar transaction next year on 12/31/2021. But that's cutting it pretty close and doesn't leave any room for subsequent years.
I also know that I can't just use another one of my IRAs for the rollover because the IRS aggregates all your IRAs for most tax purposes.
But I started thinking, why not use my IRA this year, my wife's IRA next year, and so on. I would think we are each individually entitled to one non-taxable roll-over per year, even though we file a joint return. But I can't find anything authoritative on this question. Does anyone know?
Also just curious, for those of you who do this, how do you get around the "one rollover per year" rule? I suppose if I had done it much earlier in December that would give me plenty of time for subsequent years.